(+)-(2S,3S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3-phenylcarbonyloxy-2-pentyl-tetrahydrofuran

Base Information

Chemical Name:(+)-(2S,3S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3-phenylcarbonyloxy-2-pentyl-tetrahydrofuran
CAS No.:951133-93-0
Molecular Formula:C₂₃H₃₈O₄Si
Molecular Weight:406.638
Hs Code.:

Synonyms:(+)-(2S,3S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3-phenylcarbonyloxy-2-pentyl-tetrahydrofuran

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+)-(2S,3S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3-phenylcarbonyloxy-2-pentyl-tetrahydrofuran

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Technology Process of (+)-(2S,3S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3-phenylcarbonyloxy-2-pentyl-tetrahydrofuran

There total 13 articles about (+)-(2S,3S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3-phenylcarbonyloxy-2-pentyl-tetrahydrofuran which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

: 951133-92-9
(+)-(2S,3S,5R)-5-(tert-butyldimethylsilyloxymethyl)-2-pentyl-tetrahydrofuran-3-ol

: 65-85-0,8013-63-6
benzoic acid

: 951133-93-0
(+)-(2S,3S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3-phenylcarbonyloxy-2-pentyl-tetrahydrofuran

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃;
DOI:10.1016/j.tetlet.2007.07.058

Reference yield:

: 951133-45-2
(+)-(5S,S(S))-(4E)-4-(p-tolylsulfinyl)deca-1,3-dien-5-ol

: 951133-93-0
(+)-(2S,3S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3-phenylcarbonyloxy-2-pentyl-tetrahydrofuran

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / Et₃N; DMAP / dimethylformamide / 0 - 20 °C

2: 60 percent / NH₄OAc; H₂O₂ / (R,R)-JC catalyst / CH₂Cl₂; methanol / 48 h / 0 °C

3: imidazole; DMAP / CH₂Cl₂ / 0 - 20 °C

4: 97 percent / KOOt-Bu / tetrahydrofuran / -40 - 0 °C

5: 96 percent / MgI₂ / diethyl ether / 0 - 20 °C

6: L-Selectride / tetrahydrofuran / -78 °C

7: 92 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; dmap; ammonium acetate; dihydrogen peroxide; L-Selectride; triethylamine; dicyclohexyl-carbodiimide; magnesium iodide; (R,R)-JC catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 2: Jacobsen epoxidation;
DOI:10.1016/j.tetlet.2007.07.058

Reference yield:

: 66-25-1
hexanal

: 951133-93-0
(+)-(2S,3S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3-phenylcarbonyloxy-2-pentyl-tetrahydrofuran

Guidance literature:: Multi-step reaction with 8 steps

1: LDA

2: 89 percent / Et₃N; DMAP / dimethylformamide / 0 - 20 °C

3: 60 percent / NH₄OAc; H₂O₂ / (R,R)-JC catalyst / CH₂Cl₂; methanol / 48 h / 0 °C

4: imidazole; DMAP / CH₂Cl₂ / 0 - 20 °C

5: 97 percent / KOOt-Bu / tetrahydrofuran / -40 - 0 °C

6: 96 percent / MgI₂ / diethyl ether / 0 - 20 °C

7: L-Selectride / tetrahydrofuran / -78 °C

8: 92 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; dmap; ammonium acetate; dihydrogen peroxide; L-Selectride; triethylamine; dicyclohexyl-carbodiimide; magnesium iodide; lithium diisopropyl amide; (R,R)-JC catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 3: Jacobsen epoxidation;
DOI:10.1016/j.tetlet.2007.07.058